Facile Approach to Covalent Copolypeptide Hydrogels and Hybrid Organohydrogels

Hanay, Saltuk; O’Dwyer, Joanne; Kimmins, Scott D.; Oliveira, Fernando C. S. de; Haugh, Matthew G.; O’Brien, Fergal J.; Cryan, Sally‐Ann; Heise, Andreas

doi:10.1021/acsmacrolett.8b00431

Cited by 16 publications

(8 citation statements)

References 45 publications

(59 reference statements)

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“…Urazoles are nitrogen-containing heterocycles that have been mostly used as precursors of triazolinediones (TADs) which have recently attracted attention owing to their click and click-like reactions [ 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. Urazoles can readily be oxidized to TADs by strong oxidants [ 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

Exploiting Urazole’s Acidity for Fabrication of Hydrogels and Ion-Exchange Materials

Hanay

Fallah

Senturk

et al. 2021

Gels

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In this study, the acidity of urazole (pKa 5–6) was exploited to fabricate a hydrogel in two simple and scalable steps. Commercially available poly(hexamethylene)diisocyanate was used as a precursor to synthesize an urazole containing gel. The formation of urazole was confirmed by FT-IR and 1H-NMR spectroscopy. The hydrogel was characterized by microscopy imaging as well as spectroscopic and thermo-gravimetric analyses. Mechanical analysis and cell viability tests were performed for its initial biocompatibility evaluation. The prepared hydrogel is a highly porous hydrogel with a Young’s modulus of 0.91 MPa, has a swelling ratio of 87%, and is capable of exchanging ions in a medium. Finally, a general strategy was demonstrated to embed urazole groups directly into a crosslinked material.

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Section: Introductionmentioning

confidence: 99%

Exploiting Urazole’s Acidity for Fabrication of Hydrogels and Ion-Exchange Materials

Hanay

Fallah

Senturk

et al. 2021

Gels

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“…TADs have recently attracted attention owing to their click and clicklike reactions. [8][9][10][11][12][13][14] Urazoles can readily be oxidized to TADs by strong oxidants. [15][16] Alternatively, some urazoles can be aerobically oxidized to corresponding TADs by laccase enzyme.…”

Section: Introductionmentioning

confidence: 99%

Urazole as an unorthodox functional group for fabrication of anionic hydrogels and ion-exchange materials

Hanay

Fallah

Senturk

et al. 2021

Preprint

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In this study, highly ionazable protons (pKa 5-6) of urazole were exploited to obtain an anionic hydrogel in two simple and scalable steps. Commercially available multiisocyanate, poly(hexamethylene)diisocyanate, was used to prepare urazole containing gel. Urazole formation was confirmed by FT-IR and 1H-NMR spectroscopy. The hydrogel were characterized by microscopy imaging, spectroscopic and gravimetric analysis. Mechanical analysis and cell viability test were performed for its initial biocompatibility evaluation. The prepared hydrogel is a highly porous hydrogel with a Young’s modulus of 0.91MPa, has swelling ratio of 87% and capable of exchanging ions in a medium. In this report, we demonstrated a strategy to overcome synthetic challenge of incorporating urazole into a material via precursor path rather than attempting to embeding urazole groups directly.

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“…As the double bond is preserved in the Alder–ene reaction, further functionalisation can be undertaken utilising the shifted double bond. TADs have been used to modify unsaturated polymers [32], prepare films [33], produce hydrogels [34,35] and produce crosslinked nanostructures [36]. In one example, a bis-functional TAD was applied to unsaturated fatty acids to produce crosslinked films from vegetable oils [37,38].…”

Section: Introductionmentioning

confidence: 99%

Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD)

et al. 2019

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Crosslinking of an unsaturated aliphatic polyester poly(globalide) (PGl) by bistriazolinediones (bisTADs) is reported. First, a monofunctional model compound, phenyl–TAD (PTAD), was tested for PGl functionalisation. 1H-NMR showed that PTAD–ene reaction was highly efficient with conversions up to 97%. Subsequently, hexamethylene bisTAD (HM–bisTAD) and methylene diphenyl bisTAD (MDP–bisTAD) were used to crosslink electrospun PGl fibres via one- and two-step approaches. In the one-step approach, PGl fibres were collected in a bisTAD solution for in situ crosslinking, which resulted in incomplete crosslinking. In the two-step approach, a light crosslinking of fibres was first achieved in a PGl non-solvent. Subsequent incubation in a fibre swelling bisTAD solution resulted in fully amorphous crosslinked fibres. SEM analysis revealed that the fibres’ morphology was uncompromised by the crosslinking. A significant increase of tensile strength from 0.3 ± 0.08 MPa to 2.7 ± 0.8 MPa and 3.9 ± 0.5 MPa was observed when PGI fibres were crosslinked by HM–bisTAD and MDP–bisTAD, respectively. The reported methodology allows the design of electrospun fibres from biocompatible polyesters and the modulation of their mechanical and thermal properties. It also opens future opportunities for drug delivery applications by selected drug loading.

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Facile Approach to Covalent Copolypeptide Hydrogels and Hybrid Organohydrogels

Cited by 16 publications

References 45 publications

Exploiting Urazole’s Acidity for Fabrication of Hydrogels and Ion-Exchange Materials

Exploiting Urazole’s Acidity for Fabrication of Hydrogels and Ion-Exchange Materials

Urazole as an unorthodox functional group for fabrication of anionic hydrogels and ion-exchange materials

Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD)

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